A western boy, Murray Bert Olmstead began his career as a junior with Moose Jaw in the Saskatchewan league. He played for two years and then turned pro. The Montreal Canadiens assigned him to Kansas City of the United States Hockey League, but his rights were traded to Chicago and in 1948-49 he made his NHL debut with the Hawks, playing on a line with Metro Prystai and Bep Guidolin. The next year, his first full season in the league, he scored 20 goals and established himself as a bona fide NHLer. The 1950-51 year was both confusing and important to Olmstead in establishing himself in the NHL. On December 10, 1950, he was traded to Detroit, but just nine days later the Red Wings sent him back to Montreal. It was there that he stayed for the next eight years, winning the Stanley Cup three times in succession with the Habs.

For much of his time in Montreal he played on the number one line. Initially this meant playing with Elmer Lach and Maurice Richard, succeeding the retired Toe Blake on the famed scoring line. Later he was on the left wing with Jean Beliveau and Boom Boom Geoffrion, and, surprisingly, it was his more famous linemates who claimed Bert was the key to the combination.

Although he wasn't known as a scorer or point-getter, Olmstead did set an NHL record for most assists in a season with 56 in 1955-1956, a record that wasn't broken until Jean Beliveau collected 61 five years later. He also scored eight points in a game, tying a league record, but most of all he was known for his leadership qualities, for getting the most out of his teammates and inspiring those around him to play better. As Punch Imlach later said, he coached himself.

Olmstead's departure from Montreal wasn't pleasant. After the 1957-58 season, the Montreal doctors told him he had no strength left in his knees and the Habs left him unprotected in the Intra-League Draft. Toronto coach Billy Reay pounced at the chance to claim him, and just like that Olmstead went from the Canadiens to the dreaded enemy, the Maple Leafs.

In Toronto, his career was rejuvenated and his experience proved a catalyst to the team's improved fortunes as the 1950s became the 1960s. Early in the 1958-59 season, assistant general manager Punch Imlach fired coach Reay and installed himself as coach, immediately naming Olmstead his playing assistant. In day-to-day life, this meant that Imlach would handle the club and coach games and Olmstead would run the practices. The season culminated with one of the greatest stretch runs to qualify for the playoffs, and the Leafs made it to the finals before losing to Montreal.

After three months as playing assistant, Olmstead resigned as assistant and kept to his on-ice responsibilities with his linemates Mahovlich and Bob Nevin. The team made it to the finals in 1960 and two years later won the Stanley Cup, in large measure because of Olmstead's role on the team and despite his having missed two months of the season with a badly broken shoulder.

That summer Olmstead was shocked to learn he had been claimed by the New York Rangers in the Intra-League Draft, exposed by Toronto just as Montreal had exposed him a few years earlier. He refused to report to New York, and then the Canadiens phoned him and promised that if he reported, they'd make a trade within a month. He demanded the trade be made right away or not at all and the deal never materialized. Olmstead's career was over in a flash.

He later became coach of the hapless Oakland Seals during that team's first year of operation, but after a dismal season he never returned behind the bench, although he was at one time rumoured to be John McLellan's replacement in Toronto in the early 1970s. He was inducted into the Hall of Fame in 1985.